Title:
LACTONE COMPOUNDS AND METHODS OF MAKING AND USING SAME
Document Type and Number:
WIPO Patent Application WO/2016/069542
Kind Code:
A3
Abstract:
Provided herein are lactone compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as inhibitors of serine hydrolases, such as ABHD16A. Furthermore, the subject compounds and compositions may be useful for the treatment of, for example, PHARC and other neuroinflammatory diseases.
Inventors:
CRAVATT BENJAMIN F (US)
KAMAT SIDDHESH S (US)
PARSONS WILLIAM H (US)
HOWELL AMY R (US)
CAMARA KADDY (US)
ANDERSON AMY (US)
KAMAT SIDDHESH S (US)
PARSONS WILLIAM H (US)
HOWELL AMY R (US)
CAMARA KADDY (US)
ANDERSON AMY (US)
Application Number:
PCT/US2015/057490
Publication Date:
August 04, 2016
Filing Date:
October 27, 2015
Export Citation:
Assignee:
SCRIPPS RESEARCH INST (US)
UNIV CONNECTICUT (US)
UNIV CONNECTICUT (US)
International Classes:
C07D305/12; A61K31/337; A61K31/365; C07D305/10
Domestic Patent References:
| WO2013177492A2 | 2013-11-28 | |||
| WO2013083724A1 | 2013-06-13 |
Foreign References:
| US20060258620A1 | 2006-11-16 |
Other References:
MARTINEZ, ISAMIR ET AL.: "Unusual, Strained Heterocycles: 3-Alkylidene-2-methyleneoxetanes from Morita-Baylis-Hillman-type Adducts", ORGANIC LETTERS, vol. 5, no. 4, 2003, pages 399 - 402
MULZER, MICHAEL ET AL.: "Carbonylative enantioselective meso-desymmetrization of cis-epoxides to trans-beta-lactones: effect of salen-ligand electronic variation on enantioselectivity", CHEMICAL COMMUNICATIONS, vol. 50, no. 69, 14 July 2014 (2014-07-14), pages 9842 - 9845
SCHEROWSKY, GUENTER ET AL.: "Stereoselective Synthesis of Optically Active Di- and Trisubstituted Oxetanones as Chiral Dopants to Induce Ferroelectricity in Liquid Crystals", CHIMIA INTERNATIONAL JOURNAL FOR CHEMISTRY, vol. 47, no. 1-2, 1993, pages 19 - 21
NOEL, AMANDINE ET AL.: "Chemistry of the B-Thiolactones: Substituent and Solvent Effects on Thermal Decomposition and Comparison with the beta-Lactones", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 79, 9 April 2014 (2014-04-09), pages 4068 - 4077
MULZER, MICHAEL ET AL.: "Carbonylation of cis-Disubstituted Epoxides to trans -beta-Lactones: Catalysts Displaying Steric and Contrasteric Regioselectivity", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 79, 9 October 2014 (2014-10-09), pages 11851 - 1186
WEDLER, CHRISTINE ET AL.: "Synthesis of beta-Lactones via a Spontaneous Intramolecular Cyclization of O-Lithiated Phenyl beta-Hydroxyalkanoates Obtained by Aldolization of Ketones or Aldehydes with Lithium Enolates of Phenyl Esrers", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 60, 1995, pages 758 - 760
WEDLER, CHRISTINE ET AL.: "One-Step Synthesis of beta-Lactones by Aldolization of Ketones or Aldehydes with 1-Acylbenzotriazoles`", LIEBIGS. ANN., vol. 1996, no. 6, 1996, pages 881 - 885
LALL, MANJINDER S. ET AL.: "Serine and Threonine beta-Lactones:A New Class of Hepatitis A Virus 3C Cysteine Proteinase Inhibitors", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 67, 2002, pages 1536 - 1547
SHINDO, MITSURU ET AL.: "Novel synthesis of ynolates via the cleavage of ester dianions: alpha-Bromo and alpha, alpha-dibromo esters as precursors", TETRAHEDRON, vol. 54, 1998, pages 2411 - 2422
ARONICA, LAURA ANTONELLA ET AL.: "Synthesis of functionalised beta-lactones via silylcarbocyclisation/desilylation reactions of propargyl alcohols", TETRAHEDRON, vol. 66, 2010, pages 265 - 273
MULZER, MICHAEL ET AL.: "Enantioenriched beta-lactone and aldol-type products from regiodivergent carbonylation of racemic cis-epoxides", CHEMICAL SCIENCE, vol. 5, pages 1928 - 1933
COMPTON, COREY L. ET AL.: "Antibacterial Activity of and Resistance to Small Molecule Inhibitors of the ClpP Peptidase", ACS CHEMICAL BIOLOGY, vol. 8, 2013, pages 2669 - 2677
BEJOT, ROMAIN ET AL.: "`alpha-Haloenol Acetates: Versatile Reactants for Oxetan-2-one, Azetidin-2-one and Isoxazolidin-5-one Synthesis", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2007, 2007, pages 101 - 107
KULL, THOMAS ET AL.: "Catalytic asymmetric synthesis of trans-configured beta-lactones: cooperation of Lewis acid and ion pair catalysis", CHEMISTRY-A EUROPEAN JOURNAL, vol. 16, 2010, pages 9132 - 9139
DEKKER, FRANK J. ET AL.: "Small-molecule inhibition of APT1 affects Ras localization and signaling", NATURE CHEMICAL BIOLOGY, vol. 6, 2010, pages 449 - 456
KAMAT, SIDDHESH S. ET AL.: "Immunomodulatory lysophosphatidylserines are regulated by ABHD16A and ABHD12 interplay", NATURE CHEMICAL BIOLOGY, vol. 11, no. 2, 12 January 2015 (2015-01-12), pages 164 - 171
MULZER, MICHAEL ET AL.: "Carbonylative enantioselective meso-desymmetrization of cis-epoxides to trans-beta-lactones: effect of salen-ligand electronic variation on enantioselectivity", CHEMICAL COMMUNICATIONS, vol. 50, no. 69, 14 July 2014 (2014-07-14), pages 9842 - 9845
SCHEROWSKY, GUENTER ET AL.: "Stereoselective Synthesis of Optically Active Di- and Trisubstituted Oxetanones as Chiral Dopants to Induce Ferroelectricity in Liquid Crystals", CHIMIA INTERNATIONAL JOURNAL FOR CHEMISTRY, vol. 47, no. 1-2, 1993, pages 19 - 21
NOEL, AMANDINE ET AL.: "Chemistry of the B-Thiolactones: Substituent and Solvent Effects on Thermal Decomposition and Comparison with the beta-Lactones", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 79, 9 April 2014 (2014-04-09), pages 4068 - 4077
MULZER, MICHAEL ET AL.: "Carbonylation of cis-Disubstituted Epoxides to trans -beta-Lactones: Catalysts Displaying Steric and Contrasteric Regioselectivity", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 79, 9 October 2014 (2014-10-09), pages 11851 - 1186
WEDLER, CHRISTINE ET AL.: "Synthesis of beta-Lactones via a Spontaneous Intramolecular Cyclization of O-Lithiated Phenyl beta-Hydroxyalkanoates Obtained by Aldolization of Ketones or Aldehydes with Lithium Enolates of Phenyl Esrers", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 60, 1995, pages 758 - 760
WEDLER, CHRISTINE ET AL.: "One-Step Synthesis of beta-Lactones by Aldolization of Ketones or Aldehydes with 1-Acylbenzotriazoles`", LIEBIGS. ANN., vol. 1996, no. 6, 1996, pages 881 - 885
LALL, MANJINDER S. ET AL.: "Serine and Threonine beta-Lactones:A New Class of Hepatitis A Virus 3C Cysteine Proteinase Inhibitors", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 67, 2002, pages 1536 - 1547
SHINDO, MITSURU ET AL.: "Novel synthesis of ynolates via the cleavage of ester dianions: alpha-Bromo and alpha, alpha-dibromo esters as precursors", TETRAHEDRON, vol. 54, 1998, pages 2411 - 2422
ARONICA, LAURA ANTONELLA ET AL.: "Synthesis of functionalised beta-lactones via silylcarbocyclisation/desilylation reactions of propargyl alcohols", TETRAHEDRON, vol. 66, 2010, pages 265 - 273
MULZER, MICHAEL ET AL.: "Enantioenriched beta-lactone and aldol-type products from regiodivergent carbonylation of racemic cis-epoxides", CHEMICAL SCIENCE, vol. 5, pages 1928 - 1933
COMPTON, COREY L. ET AL.: "Antibacterial Activity of and Resistance to Small Molecule Inhibitors of the ClpP Peptidase", ACS CHEMICAL BIOLOGY, vol. 8, 2013, pages 2669 - 2677
BEJOT, ROMAIN ET AL.: "`alpha-Haloenol Acetates: Versatile Reactants for Oxetan-2-one, Azetidin-2-one and Isoxazolidin-5-one Synthesis", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2007, 2007, pages 101 - 107
KULL, THOMAS ET AL.: "Catalytic asymmetric synthesis of trans-configured beta-lactones: cooperation of Lewis acid and ion pair catalysis", CHEMISTRY-A EUROPEAN JOURNAL, vol. 16, 2010, pages 9132 - 9139
DEKKER, FRANK J. ET AL.: "Small-molecule inhibition of APT1 affects Ras localization and signaling", NATURE CHEMICAL BIOLOGY, vol. 6, 2010, pages 449 - 456
KAMAT, SIDDHESH S. ET AL.: "Immunomodulatory lysophosphatidylserines are regulated by ABHD16A and ABHD12 interplay", NATURE CHEMICAL BIOLOGY, vol. 11, no. 2, 12 January 2015 (2015-01-12), pages 164 - 171
Attorney, Agent or Firm:
HOSTETLER, Michael J. (650 Page Mill RoadPalo Alto, California, US)
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